Crazy Cupid
by existential1rony
Summary: An incredibly weird and crazy arrest on Valentine's Day allows Jay and Hailey to have some interesting topics to discuss once it's over. Just a lighthearted one-shot in typical Upstead fare.


It was Valentine's Day at the 21st and the Intelligence Unit were trying to track down a known drug dealer who was monopolizing the West Side. The team had already been in for a long day and night and they never thought they'd make it home or to their extracurricular activities if they were lucky enough to have them. By the grace of Cupid, a call came in to Sergeant Platt's desk tipping them off to the whereabouts of Wayman Thomas, their suspect. They all geared up and got ready to raid the address they were given.

Voight had it setup for Jay, Hailey, and Kevin to breach the front-door with him while Adam and Vanessa would monitor the back entrance to limit chances of escape. Right before they kicked in the door, they heard a woman yelling, sounding clearly enraged.

"You stupid dick, they're coming for you now. I don't care! Try surviving a night in lock up with that hard-on."

"You crazy! HELP, somebody HELP!" came the sound of a male voice.

Voight glanced at his team on the front stairs giving Jay the nod to bash in the door and started yelling "Go, Go, Go!" over the radio, signaling for Adam and Vanessa to join from the back. They needed all hands on deck now since they had no idea what they were dealing with.

They cleared the first floor as a unit to find nothing amiss, but continued to hear the arguing from upstairs. They slowly went one at a time, splitting up again at the top of the stairs to check each bedroom.

"Clear!" Jay and Hailey confirmed from their first room with Voight and Vanessa close behind.

They were continuing down the hall when they heard Adam yell out, "OH FOR THE LOVE OF GOD! WHAT THE FUCK?"

Closely followed by Kevin's softer, "Holy Shit!"

Everyone else came running to meet them and all six pairs of eyes gaped in shock at what was going on in the master bedroom all the way at the end of the house. There was their suspect, Wayman Ellis, on his knees handcuffed with his arms behind his back against the king bed front leg post. He was naked, aside from nipple clamps hanging off of him and sporting what looked to be a painful erection. A woman slightly younger than him was hovering over him about a foot away, both still screaming at each other.

"You crazy bitch, you're insane!" Wayman screamed.

"Shut the fuck up player, you're getting what's coming to you!" she yells back as she takes the drumstick she's holding and whacks his erection with it, causing Wayman to yelp in pain.

"You guys gotta help me, she's crazy! She overdosed me with a Viagra cocktail after promising me some kink and she's now been doing this for hours!"

The team finally snaps out of their shock enough and Adam and Kevin run over to restrain the angry woman.

"Fuck you! That's what you get for fucking every hoe up the block behind my back then lying about it!" she flails in Adam and Kevin's arms while Vanessa comes over to cuff her.

"Wayman Ellis, you're under arrest for possession and distribution… I'd say we'd cuff you, but it looks like your girlfriend over here took care of that already." Voight says in his gruff voice, clearly amused by the situation.

Jay looks at Hailey as they snicker together and start making their way over to handle Wayman. "5021 Henry, roll an ambulance and patrol car to 1100 West Jackson, offender has a bit of a predicament." Hailey says into her radio.

Hailey grabs a sheet off the bed and hands it to Jay so he can wrap it around Wayman as they set him free from the bed post only to re-cuff him.

"You guys really arresting him?" Wayman's girl asks.

"Of course! What did you think? You made the tip yourself!" Jay responds to her while trying to hold back a chuckle at his unrealized pun.

"Shit! Baby, I'm sorry, I was just so jealous!" she says to Wayman, clearly down a bit from her high. Wayman just nods his head at her.

They all make their way outside with both offenders once the ambulance and backup arrives. As the paramedics take care of Wayman, patrol lets his now distraught girlfriend say goodbye before they put her in the squad car.

"I love you, Way, I'm sorry! I'll make it up to you once we get out, I promise!"

"I love you too, baby!" Wayman replies before they load him into the ambo.

The team continues to stare on in disbelief, still shocked by the varying events of the past thirty minutes.

"31 years on the job, just when you think you've seen it all…"Voight says.

"Love makes you do crazy things!" Kevin jokes.

"I need a drink…" Vanessa responds as they all nod their heads in agreement, more than ready to get as far away from this scene as possible.

* * *

A couple hours later Jay and Hailey are finally back at her place and ready to unwind from all the crazy. Vanessa decided to still give it a go with her online date, even though it ended up being much later. Adam was going to keep Kim company and see if he could lift her spirits some, the miscarriage still fresh in their minds. And Kevin had plans to go to a singles mixer that Jay and Hailey happily declined. The quiet night was turning out to be just fine for the two of them, neither wanting to admit there was no one or where else they'd rather be with or at anyway.

"Working till 10pm, Grubhub, and literal chill, what more can a guy want on Valentine's Day?" Jay said as they sat around Hailey's kitchen island eating their Chinese and sipping their beers.

"Shutup, this is probably your hottest Valentine's ever!" Hailey replied.

"I've definitely had worse. I spent one in Afghanistan so this is at least better than that!" he teases as she rolls her eyes.

"You're such a jerk!"

He smiles as he takes another sip of his beer, staring over the bottle at her. "…You are the hottest though!"

He smirks to himself as he notices the blush she can't hide.

"Yeah well, now you're just sounding like that crazy girlfriend, trying to make amends for your jerk behavior."

"Stop, my eyes have still not fully recovered, Hailey!"

"You're telling me. I think I may have to burn mine, or do like six shots to forget!"

"Let's do it!" Jay says eagerly.

"What? You serious right now?" Hailey asks stunned, it's not often Jay wants to get _drunk,_ drunk anymore.

"C'mon, it's Friday. We're supposed to be off all weekend, and you already turned down going to Molly's. So let's just have our own party, we deserve it."

She smiles at his excitement. "Alright… but just remember, I'm Greek, so I can still outdo your light-weight ass."

Jay scoffs at her. "I'm Irish, in what world would that happen?"

She gives him one of her _seriously_ looks. "St. Paddy's Day, 2018…"

"Oh c'mon, I didn't eat all day. And I did more Car-bombs than you!"

"I did more shots than you!"

"Alright. It's on then, Upton!" he grins as he grabs her good tequila and two shot glasses.

She nods at him as he pours their shots and they raise their glasses over her counter together.

"To Cupid bringing even those two nutjobs from today together, may we all _NOT_ find that!" Jay jokes as they laugh and say, "Cheers" downing their shots together.

After a little more of jovial conversation and three shots down they had migrated over to the living room to get more comfortable. Jay kicked off his shoes and stretched his legs under her coffee table, as Hailey sat next to him on the couch with her legs tucked under her. It wasn't a great position to see the TV, but perfect for when they did another shot or for when she wanted to secretly glance at Jay when he wasn't looking.

It had been a few months now since she almost told him she loved him when he was getting released from the hospital and the subject never came back up. Their cases had been so wild and things had been so dark, most recently Kim's miscarriage, that it just never seemed like the right time. Jay asked her about it again about a week or so after he got out, but she brushed it off and he hasn't pushed her since. She sometimes wonders if he suspects what she wanted to tell him, but a part of her hopes he doesn't because then it would be slightly upsetting on why he never wanted to circle back to it. She still has the fear in the back of her mind that he doesn't feel the same way, but then she remembers him following her after Darius, and all the concerned and heated looks he gives her, not to mention his flirting has seemed to tick up a notch in their rare lighter moments, like tonight.

While Hailey sits there lost in her thoughts over Jay, he's lost in his over her. He can't help but feel this really has been his best Valentine's Day ever… not because all of his past ones were shitty, just because he gets to spend this one with Hailey. He loves when she's happy and carefree and wishes he could see that side of her more. But he's extra grateful he's one of the ones who can bring it out. Like him, she's been through so much in her life and he just wants them to finally give in and admit that they make the other happy. He suspects she was going to tell him how she felt when he was leaving the hospital, but she dropped the subject real fast after he almost answered Bobby's phone call. He doesn't blame her; he's put her through a lot. And he hasn't pushed since she's never brought it back up. He just wishes she'd realize he'd do anything for her, including trying to stop himself from foolishly getting in harm's way. He grabs the bottle and starts pouring them another shot as she stares at him wide-eyed.

"Oh, you ready to admit defeat there?" he chuckles at her and she giddily laughs back, both clearly feeling it now.

"Never, Halstead!"

"Cheers" they say again as they clink their glasses together and down another.

Hailey lays her head back on the cushion as they continue to stare at the other and smile. The alcohol must be making her bolder because the words are out of her mouth before her brain can stop them.

"So, did you have a hot date tonight that work killed?"

He looks at her surprised she asked. "What? Like who?"

"I don't know, you could have gone on Tinder or something." She shrugs.

"Not really my style, Hailey, you know that."

"Yeah, but it's Valentine's Day, makes people do all crazy things."

He laughs. "I'm good!" he says hoping to get the point across to her that she's the company he prefers.

"Was Camilla the last person you were with?" she asks softly, genuinely curious because she wants to know, but is also scared to.

"Wow, we're getting real personal tonight, huh?"

"I'm sorry, you don't have to answer. Quarter bottle of tequila and I get loose."

Jay raises his eyebrow at her. "Oh yeah?"

She blushes realizing how that sounded. "My words, I meant with my words…"

"She was…" he says softly, drifting off giving Hailey a minute for the realization to dawn on her. She nods back at him slowly, a small smile on her face. Since she's being so bold, Jay decides he can as well. "I'd ask who you were last with, but I think I still know the answer. I'm still kind of shocked over it, always thought you'd choose me over Adam." He teases.

"Well I'd have slept with _you_, but you know you had to go and get shot… the first time!" she jokes back.

"So you're saying I would have been your first option?"

"Jay… you're my only option, you know that…" she quietly replies, realizing how it sounds once she sees the look of awe on his face. She quickly tries to backtrack, "I mean…"

Jay lunges forward, kissing her gently and instantly silencing her. It takes her a second but soon she's melting into his lips and touch, her hands tightly grabbing the collar of his t-shirt. Jay knocks off the tequila bottle in between them on the couch and softly pushes her back so they're both lying flat. Their kiss rapidly getting more heated as Hailey opens her mouth to him and Jay's tongue duels with hers. After a few breathless minutes Jay finally pulls back and leans his forehead against hers, both of them unable to control the smiles that form.

"Hailey, you're the only one I've wanted for years…" he whispers hoarsely, his voice laced with yearning and lust.

"Me too…" she replies, equally as worked up, her hands stroking his cheeks and she brings his lips back down to hers.

A few minutes pass before Jay slowly starts unbuttoning Hailey's shirt and moving his lips down her neck and chest as she pulls his shirt off completely. They both moan at the contact, ecstatic that they're finally at this point.

"You know, I have some handcuffs in my bedroom too." She whispers as she starts undoing his belt.

He groans. "You're not gonna leave me high and dry like Wayman's girlfriend did are you?"

"Depends on how bad of a boy you are!" she jokes back.

That's all it took for Jay to be done with the teasing as he wrapped his arms around her waist and carried her to the bedroom. Once they reached the bed things got progressively heated and they both sighed as Jay slowly entered Hailey's warmth. Neither of them had ever felt anything so right before, it was like they were finally home. As Jay started to move slowly, Hailey decided to confess before she got too worked up, already gasping.

"Jay, when you were in the hospital, I wanted to tell you that it made me realize that I'm in love with you…"

He smiled warmly at her, his heart elated. "I know… I love you too!"

He rubbed his nose against hers before they started kissing again and his hips picked up the pace, ending all conversation for the next couple of hours. Once they were wiped out completely, Hailey layed in Jay's arms with her head tucked into his chest, the Winter moonlight giving off a light romantic glow as it seeped through the drapes.

Jay was the most content he'd ever been. As he softly stroked Hailey's arm he titled his head to hers and said, "Remind me to send a box of chocolates to Wayman's jail."

Her laughter filled the room. "Happy Valentine's Day! I hope this was your hottest now."

"Definitely, my forever Valentine!"

Two years later Jay made those words official, they even added them to their vows...

* * *

_[A/N: Just another quick one-shot. I'm not the biggest fan of Valentine's Day, but figured Upstead needed some cliche loving! ;) Hope you enjoy and thanks for the support.] _


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